Process for producing fluorine-containing sulfonylimide compound

Abstract

In this process for producing a fluorine-containing sulfonylimide compound, a process for producing a fluorine-containing sulfonylimide compound ((Rf 1 SO 2 )(Rf 2 SO 2 ) 2 N.M) is employed that comprises a first step of obtaining a reaction liquid by reacting a perfluoroalkylsulfonyl fluoride (Rf 1 SO 2 F) with ammonia, a second step of obtaining a mixture containing an alkaline metal salt of a perfluoroalkylsulfonamide (Rf'SO 2 NH.M) by reacting the reaction liquid with at least one type of alkaline metal compound selected from among hydroxides, carbonates and bicarbonates of alkaline metals M of either Li, Na or K, and a third step of reacting the mixture with a perfluoroalkylsulfonyl halide (Rf 2 SO 2 X), wherein Rf 1 and Rf 2 represent linear or branched perfluoroalkyl groups having 1 to 4 carbon atoms, and X represents fluorine or chlorine.

1 . A process for producing a fluorine-containing sulfonylimide compound represented by the following formula (1), comprising:
 a first step of obtaining a reaction liquid by reacting a perfluoroalkylsulfonyl fluoride represented by the following formula (2) with ammonia,   a second step of obtaining a mixture containing an alkaline metal salt of a perfluoroalkylsulfonamide represented by the following formula (3) by reacting the reaction liquid with at least one type of alkaline metal compound selected from among hydroxides, carbonates and bicarbonates of alkaline metals M of either Li, Na or K, and   a third step of reacting the mixture with a perfluoroalkylsulfonyl halide represented by the following formula (4):
   (Rf 1 SO 2 )(Rf 2 SO 2 )N.M   (1)
 
   Rf 1 SO 2 F   (2)
 
   Rf 1 SO 2 NH.M   (3)
 
   Rf 2 SO 2 X   (4)
 
   
       (wherein, in the formulas (1) to (4), Rf 1  and Rf 2  represent linear or branched perfluoroalkyl groups having 1 to 4 carbon atoms, and in formula (4), X represents fluorine (F) or chlorine (Cl)). 
     
     
         2 . The process for producing the fluorine-containing sulfonylimide compound represented by formula (1) according to  claim 1 , comprising:
 a first step of obtaining a reaction liquid containing an ammonium salt of a perfluoroalkylsulfonamide represented by the following formula (5) and ammonium fluoride by reacting the perfluoroalkylsulfonyl fluoride represented by formula (2) with ammonia,   a second step of obtaining a mixture containing an alkaline metal salt of the perfluoroalkylsulfonamide represented by formula (3) and an alkaline metal fluoride represented by the following formula (6) by reacting the reaction liquid with at least one type of alkaline metal compound selected from among hydroxides, carbonates and bicarbonates of alkaline metal elements M of either Li, Na or K, and   a third step of reacting the mixture with the perfluoroalkylsulfonyl halide represented by formula (4):
   Rf 1 SO 2 NH.NH 4    (5)
 
   MF   (6)
 
   
       (wherein, in formula (5), Rf 1  represents a linear or branched perfluoroalkyl group having 1 to 4 carbon atoms). 
     
     
         3 . The process for producing a fluorine-containing sulfonylimide compound according to  claim 1 , wherein,
 in the first step, the ammonia is aqueous ammonia and the resulting reaction liquid is an aqueous solution, and   in the second step, the reaction between the reaction liquid and the alkaline metal compound is carried out in the aqueous solution.   
     
     
         4 . The process for producing a fluorine-containing sulfonylimide compound according to  claim 1 , further comprising a fourth step of recovering ammonia generated in the second step and supplying to the first step. 
     
     
         5 . The process for producing a fluorine-containing sulfonylimide compound according to  claim 1 , wherein the concentration of the aqueous ammonia is within the range of 1% to 50%. 
     
     
         6 . The process for producing a fluorine-containing sulfonylimide compound according to  claim 1 , wherein the molar amount of the aqueous ammonia is within the range of 3 to 20 times that of the perfluoroalkylsulfonyl fluoride. 
     
     
         7 . The process for producing a fluorine-containing sulfonylimide compound according to  claim 1 , wherein the temperature of the reaction between the perfluoroalkylsulfonyl fluoride and the aqueous ammonia is within the range of 0° C. to 70° C.